Synthesis, structural and pharmacological characterizations of CIC, a novel α-conotoxin with an extended n-terminal tail

Journal Publication ResearchOnline@JCU
Giribaldi, Julien;Haufe, Yves;Evans, Edward R.J.;Wilson, David T.;Daly, Norelle L.;Enjalbal, Christine;Nicke, Annette;Dutertre, Sébastien
Abstract

Cone snails are venomous marine predators that rely on fast-acting venom to subdue their prey and defend against aggressors. The conotoxins produced in the venom gland are small disulfide-rich peptides with high affinity and selectivity for their pharmacological targets. A dominant group comprises α-conotoxins, targeting nicotinic acetylcholine receptors. Here, we report on the synthesis, structure determination and biological activity of a novel α-conotoxin, CIC, found in the predatory venom of the piscivorous species Conus catus and its truncated mutant Δ-CIC. CIC is a 4/7 α-conotoxin with an unusual extended N-terminal tail. High-resolution NMR spectroscopy shows a major influence of the N-terminal tail on the apparent rigidity of the three-dimensional structure of CIC compared to the more flexible Δ-CIC. Surprisingly, this effect on the structure does not alter the biological activity, since both peptides selectively inhibit α3β2 and α6/α3β2β3 nAChRs with almost identical sub- to low micromolar inhibition constants. Our results suggest that the N-terminal part of α-conotoxins can accommodate chemical modifications without affecting their pharmacology.

Journal

Marine Drugs

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Volume

19

ISBN/ISSN

1660-3397

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Issue

3

Pages Count

11

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Publisher

Molecular Diversity Preservation International

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EISSN

N/A

DOI

10.3390/md19030141